| 1. Round | 30/08/2008 | Roda JC Kerkrade | - | FC Twente | 1:1 | ||||
| 3. Round | 21/09/2008 | FC Volendam | - | FC Twente | 1:2 | ||||
| 4. Round | 27/09/2008 | FC Twente | - | De Graafschap | 3:0 |  |
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| 5. Round | 05/10/2008 | FC Utrecht | - | FC Twente | 3:0 | ||||
| 7. Round | 26/10/2008 | Vitesse | - | FC Twente | 0:2 | ||||
| 9. Round | 01/11/2008 | FC Twente | - | AFC Ajax | 0:2 | ||||
| 10. Round | 09/11/2008 | AZ Alkmaar | - | FC Twente | 3:0 | ||||
| 11. Round | 16/11/2008 | FC Twente | - | Feyenoord | 1:1 | ||||
| 12. Round | 22/11/2008 | FC Twente | - | sc Heerenveen | 6:0 | ||||
| 14. Round | 06/12/2008 | FC Twente | - | Sparta Rotterdam | 6:2 | ||||
| 15. Round | 14/12/2008 | FC Groningen | - | FC Twente | 1:4 | ||||
| 18. Round | 17/01/2009 | FC Twente | - | Vitesse | 2:1 |
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